7474-64-8Relevant academic research and scientific papers
Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy
Chen, Yate,Ding, Zhengtian,Wang, Yiming,Liu, Wenfeng,Kong, Wangqing
supporting information, p. 5273 - 5278 (2021/02/03)
An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.
Bidentate NHC-Cobalt Catalysts for the Hydrogenation of Hindered Alkenes
Wei, Zeyuan,Wang, Yujie,Li, Yibiao,Ferraccioli, Raffaella,Liu, Qiang
, p. 3082 - 3087 (2020/10/02)
Herein, we report a series of easily accessible bidentate N-heterocyclic carbene (NHC) cobalt catalysts, which enable the hydrogenation of hindered alkenes under mild conditions. The four-coordinated bidentate NHC-Co(II) complexes were characterized by X-ray diffraction, elemental analysis, ESI-HRMS, and magnetic moment measurements, revealing a distorted-tetrahedral geometry and a high-spin configuration of the metal center. The activity of the in situ formed catalytic system, which was obtained from easily available NHC precursors, CoCl2, and NaHBEt3, was identical with those of well-defined NHC-cobalt catalysts. This highlights the potential utility of this reaction system.
Construction of Halofunctionalized Indenes via a Cascade Prins-Nazarov Cyclization Promoted by Dual Roles of BX3
Lee, Yong Rok,Sultana, Sabera
, p. 927 - 941 (2020/01/25)
Halofunctionalization of various unactivated arylalkynes to the corresponding 1H-indenes in the presence of a particular class of carboxaldehydes and boron trihalides (BX3, X=F, Cl, Br, I) is described. A diverse array of halofunctionalized indenes substituted with a heterocycle has been synthesized regioselectively with BX3 as a promotor for the carbocyclization and a source of X? for halogenation. This reaction proceeds via a formal halogenative [4+1] cycloaddition between arylalkynes and carboxaldehydes promoted by boron trihalides to generate halofunctionalized indenes. The usefulness of the halofunctionalized indenes was demonstrated by their conversion to other derivatives via coupling, nucleophilic substitution, and oxidation. (Figure presented.).
Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of (Z)- and (E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives
Jongcharoenkamol, Jira,Chuathong, Patsapon,Amako, Yuka,Kono, Masato,Poonswat, Kasam,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 13184 - 13210 (2018/11/02)
Starting from bromo/iodobenzaldehyde derivatives, the corresponding (Z)- and (E)-(2-stilbenyl)methanols could be prepared in 2-5 steps via Pd-catalyzed cross-coupling reactions (Sonogashira and Heck reactions) followed by aryllithium/aryl Grignard addition. For the (E)-stilbenes, subsequent acid-mediated cyclization using p-TsOH immobilized on silica (PTS-Si) at low temperatures furnished the 2,3-trans-1-indanols with complete stereocontrol at the C2-C3. Further oxidization of the alcohol provided the indanones, which are structurally related to the natural product paucifloral F. At higher temperatures, 1,2- and 2,3-disubstituted indenes could be selectively prepared in good to excellent yields. On the other hand, the (Z)-stilbenes, under similar conditions (PTS-Si), did not give the indanols; only the 1,2-disubstituted indenes could be obtained. To gain further insights into the stereochemistry at C2-C3 for the (Z)-stilbenes, hydride or azide was employed as a nucleophile; the corresponding indane products were obtained with the cis stereochemistry at the C2-C3. Thus, the (Z)- or (E)-olefin geometry of the substrate directed the stereoselective indanyl cyclization to furnish the cis or trans at the C2-C3 ring junction, respectively, while reaction conditions controlled the selectivity of the product types.
Preparation method of 3-aryl-1-indanone derivate
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Paragraph 0022; 0023; 0024; 0025; 0026, (2016/10/17)
The invention discloses a preparation method of a 3-aryl-1-indanone derivate. The structural formula of the 3-aryl-1-indanone derivate is shown in the formula III. The preparation method comprises the following steps that a compound shown in the formula I reacts with a compound shown in the formula II in the presence of methyl trifluoromethanesulfonate, and therefore the 3-aryl-1-indanone derivate shown in the formula III is obtained. The preparation method of the 3-aryl-1-indanone derivate is scientific and reasonable, 3-aryl-1-indanone derivates with various substituent groups can be obtained, the raw materials are easy to obtain, no metal participates in the reaction, reaction atoms are economical, and meanwhile the preparation method has the advantages that operation is simple and convenient, the synthesis productive rate is high, the product is easy to purify, and environmental protection is achieved.
Palladium-catalyzed asymmetric reductive Heck reaction of aryl halides
Yue, Guizhou,Lei, Kaining,Hirao, Hajime,Zhou, Jianrong
, p. 6531 - 6535 (2015/06/08)
Asymmetric reductive Heck reaction of aryl halides is realized in high stereoselectivity. Hydrogen-bond donors, trialkylammonium salts in a glycol solvent, were used to promote halide dissociation from neutral arylpalladium complexes to access cationic, stereoselective pathways.
Stereoselective palladium-catalyzed α-arylation of 3-aryl-1-indanones: An asymmetric synthesis of (+)-pauciflorol F
Lee, Bong Hyang,Choi, Young Lok,Shin, Seunghoon,Heo, Jung-Nyoung
experimental part, p. 6611 - 6618 (2011/10/02)
Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these re
Toward the synthesis of caraphenol C: Substituent effect on the Nazarov cyclization of 2-arylchalcones
Zhu, Jun,Zhong, Chen,Lu, Hong-Fu,Li, Guang-Yu,Sun, Xun
, p. 458 - 462 (2008/04/01)
A mild and versatile synthesis of cis-2,3-diarylindanones using a Nazarov cyclization strategy was reported. The substituent effect on the stereochemistry of the cyclization was discussed. Georg Thieme Verlag Stuttgart.
Synthesis of α,β-unsaturated ketones by rhodium-catalyzed carbonylative arylation of internal alkynes with arylboronic acids
Ku?, Melih,Artok, ?zge Aksin,Ziyanak, Firat,Artok, Levent
experimental part, p. 2587 - 2592 (2009/04/16)
The Rh-catalyzed reaction of arylboronic acids with internal alkynes under a CO atmosphere in the presence of an acid additive afforded α,β-unsaturated ketones as the major products. Hydroacylation of internal alkynes, except in the case of diaryl acetylenes, proceeded in syn fashion, yielding the E-configured isomer. A mixture of E- and Z-isomers was obtained with diphenyl acetylene. Reactions were also highly regioselective for various nonsymmetric alkynes.
Novel one-pot approach to synthesis of indanones Through Sb(V)-catalyzed reaction of phenylalkynes with aldehydes
Saito, Akio,Umakoshi, Masaharu,Yagyu, Naomi,Hanzawa, Yuji
supporting information; experimental part, p. 1783 - 1785 (2009/04/10)
Catalytic SbF5 and the use of EtOH as an additive efficiently converted a mixture of phenylalkynes and aldehydes to indanone compounds in one pot, and the reaction stereoselectively afforded the corresponding 2,3-disubstituted indanones as a single trans-isomer.
